Herbicidal composition

ABSTRACT

An application of an N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1):  
                 
 
     wherein R 1  represents hydrogen or halogen; R 2  represents halogen and R 3  represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6 alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl, or R 2  and R 3  represent together —O—CHR 4 —C(═O)—NR 5 —, whose oxygen connected to 4-position of the benzene ring, whose nitrogen connected to 5-position of the benzene ring and wherein R 4  represents hydrogen or methyl and R 5  represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or (C1-C3 alkoxy) C1-C3 alkyl,  
     with an effective amount of an insecticidal organophosphorus compound against weeds can attain higher herbicidal effect than an application of said N-phenyltetrahydrophthalimide compound alone.

TECHNICAL FIELD

[0001] The present invention relates to a new herbicidal composition.

BACKGROUND ART

[0002] At the present time, it is known that anN-phenyltetrahydrophthalimide compound represented by Chemical Formula(1) described below has herbicidal activity (See U.S. Pat. No.4,770,695, U.S. Pat. No. 4,640,707, U.S. Pat. No. 5,062,884 and so on).

[0003] In a field of herbicide, requested are how can an application ofless amount of herbicide attain same herbicidal effect as an applicationof usual amount of it.

DISCLOSURE OF INVENTION

[0004] The present inventor has intensively studied to find out a methodfor boosting herbicidal activity of the N-phenyltetrahydrophthalimidecompound. As a result he has found that, when theN-phenyltetrahydrophthalimide compound was applied with an insecticidalorganophosphorus compound, the herbicidal activity of theN-phenyltetrahydrophthalimide compound against weeds was higher thanwhen the N-phenyltetrahydrophthalimide compound was solely applied.

[0005] Thus, the present invention provides a herbicidal composition ofthe N-phenyltetrahydrophthalimide compound represented by ChemicalFormula (1):

[0006] wherein R¹ represents hydrogen or halogen; R² represents halogenand R³ represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl, or R² and R³represent together —O—CHR⁴—C(═O)—NR⁵—, whose oxygen connected to4-position of the benzene ring, whose nitrogen connected to 5-positionof the benzene ring, wherein R⁴ represents hydrogen or methyl and R⁵represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or (C1-C3 alkoxy)C1-C3 alkyl,

[0007] and an effective amount for increasing herbicidal activity of theN-phenyltetrahydrophthalimide compound of an insecticidalorganophosphorus compound (hereinafter, referred to as the presentcomposition); and a method for controlling weeds which comprises ofapplying said N-phenyltetrahydrophthalimide compound with theinsecticidal organophosphorus compound to weeds or to a place whereweeds are growing or will grow (hereinafter referred to as the presentmethod).

[0008] The N-phenyltetrahydrophthalimide compound represented byChemical Formula (1) (hereinafter referred to as the present imidecompound) includes the compounds described below.

[0009] A compound wherein R² and R³ are together —O—CHR⁴—C(═O)—NR⁵— inChemical Formula (1), that is represented by Chemical Formula (4):

[0010] wherein

[0011] R¹, R⁴ and R⁵ are as defined above;

[0012] a compound wherein R¹ is fluorine in Chemical Formula (4);

[0013] a compound wherein R⁴ is hydrogen in Chemical Formula (4);

[0014] a compound wherein R⁵ is C3-C6 alkynyl in Chemical Formula (4);

[0015] a compound wherein R¹ is fluorine, R⁴ is hydrogen and R⁵ is C3-C6alkynyl in Chemical Formula (4);

[0016] a compound wherein R² is R²¹ and R³ is R³¹ in the ChemicalFormula (1), that is represented by Chemical Formula (5):

[0017] wherein

[0018] R¹ are as defined above, R²¹ represents halogen and R³¹represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl;

[0019] a compound wherein R¹ is fluorine in Chemical Formula (5);

[0020] a compound wherein R²¹ is chlorine in Chemical Formula (5);

[0021] a compound wherein R³¹ is (C1-C8 alkoxy)carbonyl C1-C2 alkoxy inChemical Formula (5);

[0022] a compound wherein R³¹ is C1-C6 alkynyloxy in Chemical Formula(5);

[0023] a compound wherein R³¹ is (C1-C8 alkoxy)carbonyl C2-C3haloalkenyl in Chemical Formula (5);

[0024] a compound wherein R¹ is fluorine, R²¹ is chlorine and R³¹ is(C1-C8 alkoxy)carbonyl C1-C2 alkoxy in Chemical Formula (5).

[0025] Furthermore, the present imide compound includes the compoundsdescribed below.

[0026]N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide

[0027] The insecticidal organophosphorus compound in the presentinvention includes, for example, the compounds described below.

[0028] A compound represented by Chemical Formula (6):

[0029] wherein

[0030] X¹ represents oxygen or sulfur, X² represents oxygen, sulfur ordirect bond between phosphorous atom and R⁸, R⁶ represents lower alkyl,R⁷ represents lower alkoxy, lower alkylthio, lower alkylcarbonylamino orphenyl, R⁸ represents optionally substituted alkyl, optionallysubstituted alkenyl, optionally substituted phenyl or optionallysubstituted heteroaryl;

[0031] a compound wherein X¹ is sulfur, X² is oxygen, R is C1-C4 alkyl,R⁷ is C1-C4 alkylcarbonylamino and R⁸ is optionally substituted C1-C4alkyl in the Chemical Formula (6);

[0032] a compound wherein X¹ is sulfur, X² is sulfur, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkoxy and R⁸ is optionally substituted C1-C4 alkyl in theChemical Formula (6);

[0033] a compound wherein X¹ is sulfur, X² is oxygen, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkoxy and R⁸is optionally substituted alkenyl in theChemical Formula (6);

[0034] a compound wherein X¹ is sulfur, X² is oxygen, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkoxy and R⁸ is optionally substituted phenyl in theChemical Formula (6);

[0035] a compound wherein X¹ is sulfur, X² is oxygen, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkylthio and R⁸ is optionally substituted phenyl in theChemical Formula (6);

[0036] a compound wherein X¹ is sulfur, X² is oxygen, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkoxy and R⁸ is optionally substituted pyrimidinyl in theChemical Formula (6);

[0037] a compound wherein X¹ is sulfur, X² is oxygen, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkoxy and R⁸ is optionally substituted pyridyl in theChemical Formula (6);

[0038] a compound wherein X¹ is sulfur, X² is oxygen, R⁶ is C1-C4 alkyl,R⁷ is C1-C4 alkoxy and R⁸ is optionally substituted isoxazolyl in theChemical Formula (6).

[0039] Furthermore, the insecticidal organophosphorus compound includesthe compounds described below.

[0040] O,O-dimethyl O-4-nitro-m-tolyl phosphorothioate (common name:fenitrothion);

[0041] O,O-dimethyl O-4-methylthio-m-tolyl phosphorothioate (commonname: fenthion);

[0042] O,O-diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate(common name: diazinon);

[0043] O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (commonname: chlorpyrifos);

[0044] O,S-dimethyl acetylphosphoramidothioate (common name: acephate);

[0045] S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethylO,O-dimethyl phosphorodithioate (common name: methidathion);

[0046] O,O-diethyl S-2-ethylthioethyl phosphorodithioate (common name:disulfoton);

[0047] 2,2-dichlorovinyl dimethyl phosphate (common name: dichlorvos);

[0048] O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate(common name: sulprofos);

[0049] O-4-cyanophenyl O,O-dimethyl phosphorothioate (common name:cyanophos);

[0050] O,O-dimethyl S-methylcarbamoylmethyl phosphorodithioate (commonname: dimethoate);

[0051] S-α-ethoxycarbamoylbenzyl O,O-dimethyl phosphorodithioate (commonname: phenthoate);

[0052] diethyl (dimethoxythiophosphorylthio)succinate (common name:malathion);

[0053] dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate (common name:trichlorfon);

[0054] S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl)O,O-dimethyl phosphorodithioate (common name: azinphos-methyl);

[0055] dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinyl phosphate (commonname: monocrotophos);

[0056] O,O,O′,O′-tetraethyl S,S′-methylene bis(phosphorodithioate)(common name: ethion);

[0057] S-2-ethylthioethyl O,O-dimethyl phosphorodithioate (common name:thiometon);

[0058] O,O-diethyl O-(5-phenyl-1,2-oxazol-3-yl) phosphorothioate (commonname: isoxathion);

[0059] O,O-dimethyl S-2-(1-methylcarbamoylethylthio)ethylphosphorothioate (common name: vamidothion);

[0060] O-2,4-dichlorophenyl O-ethyl S-propyl phosphorodithioate (commonname: prothiofos);

[0061] S-2-ethylsulfinyl-1-methylethyl]O,O-dimethyl phosphorothioate(common name: oxydeprofos).

[0062] The present imide compound can be produced according to theprocedures described, for example, in U.S. Pat. No. 4,770,695, U.S. Pat.No. 4,640,707, U.S. Pat. No. 5,062,884 and the others.

[0063] The present composition has herbicidal activity in the foliartreatment and the soil treatment on upland field against various weedssuch as listed below.

[0064] Polygonaceous weeds:

[0065] wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonumlapathifolium), pennsylvania smartweed (Polygonum pensylvanicum),ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleafdock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)

[0066] Portulacaceous weeds:

[0067] common purslane (Portulaca oleracea)

[0068] Caryophyllaceous weeds:

[0069] common chickweed (Stellaria media)

[0070] Chenopodiaceous weeds:

[0071] common lambsquarters (Chenopodium album), kochia (Kochiascoparia)

[0072] Amaranthaceous weeds:

[0073] redroot pigweed (Amaranthus retroflexus), smooth pigweed(Amaranthus hybridus)

[0074] Cruciferous (brassicaceous) weeds:

[0075] wild radish (Raphanus raphanistrum), wild mustard (Sinapisarvensis), shepherdpurse (Capsella bursa-pastoris)

[0076] Leguminous (fabaceous) weeds:

[0077] hemp sesbania (Sesbania exaltata), sicklepod (Cassiaobtusifolia), Florida beggarweed (Desmodium tortuosum), white clover(Trifolium repens), common vetch (Vicia sativa)

[0078] Malvaceous weeds:

[0079] velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)

[0080] Violaceous weeds:

[0081] field pansy (Viola arvensis), wild pansy (Viola tricolor)

[0082] Rubiaceous weeds:

[0083] catchweed bedstraw (cleavers) (Galium aparine)

[0084] Convolvulaceous weeds:

[0085] ivyleaf morningglory (Ipomoea hederacea), tall morningglory(Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var.integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed(Convolvulus arvensis)

[0086] Labiate weeds:

[0087] purple deadnettle (Lamium purpureum), henbit (Lamiumamplexicaule)

[0088] Solanaceous weeds:

[0089] jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)

[0090] Geraniaceae weeds:

[0091] Carolina geranium (Geranium carolinianum)

[0092] Scrophulariaceous weeds:

[0093] birdseye speedwell (Veronica persica), ivyleaf speedwell(Veronica hederaefolia)

[0094] Composite weeds:

[0095] common cocklebur (Xanthium strumarium), common sunflower(Helianthus annuus), scentless chamomile (Matricaria perforata orinodora), corn marigold (Chrysanthemum segetum), pineappleweed(Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia),giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis),Japanese mugwort (Artemisia princeps), tall goldenrod (Solidagoaltissima)

[0096] Boraginaceous weeds:

[0097] forget-me-not (Myosotis arvensis)

[0098] Asclepiadaceous weeds:

[0099] common milkweed (Asclepias syriaca)

[0100] Euphorbiaceous weeds:

[0101] sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbiamaculata)

[0102] Graminaceous weeds:

[0103] bamyardgrass (Echinochloa crus-galli), green foxtail (Setariaviridis), giant foxtail (Setaria faberi), large crabgrass (Digitariasanguinalis), goosegrass (Eleusine indica), annual bluegrass (Poaannua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua),johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downybrome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum(Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane(Sorghum vulgare)

[0104] Commelinaceous weeds:

[0105] Asiatic dayflower (Commelina communis)

[0106] Equisetaceous weeds:

[0107] field horsetail (Equisetum arvense)

[0108] Cyperaceous weeds:

[0109] rice flatsedge (Cyperus iria), purple nutsedge (Cyperusrotundus), yellow nutsedge (Cyperus esculentus)

[0110] Furthermore, the present composition also has herbicidal activityin flooding treatment of paddy fields against various weeds such aslisted below.

[0111] Graminaceous weeds:

[0112] barnyardgrass (Echinochloa oryzoides)

[0113] Scrophulariaceous weeds:

[0114] common false pimpernel (Lindernia procumbens)

[0115] Lythraceae weeds:

[0116] Indian toothcup (Rotala indica), redstem (Ammannia multiflora)

[0117] Elatinaceae weeds:

[0118] waterwort (Elatine triandra)

[0119] Cyperaceous weeds:

[0120] smallflower umbrella sedge (Cyperus difformis), hardstem bulrush(Scirpus juncoides subsp. hotarui), needle spikerush (Eleocharisacicularis), nutsedge sp. (Cyperus serotinus), water chestnut(Eleocharis kuroguwai)

[0121] Pontederiaceae weeds:

[0122] Monochoria (Monochoria vaginalis)

[0123] Alismataceae weeds:

[0124] dwarf arrowhead (Sagittaria pygmaea), arrowhead (Sagittariatrifolia), waterplantain (Alisma canaliculatum)

[0125] Potamogetonaceae weeds:

[0126] roundleaf pondweed (Potamogeton distincutus)

[0127] Umbelliferae weeds:

[0128] water dropwort sp. (Oenanthe javanica)

[0129] The present composition can also be used to control a widevariety of weeds which are growing or will grow in non-cultivated landssuch as a levee, riverbed, roadside, railroad, green field area of apark, ground, parking area, airport, industrial place (ex. factory,storage equipment), fallow field, idle land of an urban area; wood lot,grasslands, lawns, forests, and the like. The present composition alsohas herbicidal activity against various aquatic weeds, such as waterhyacinth (Eichhomia crassipes), which are growing or will grow atrivers, canals, waterways reservoirs and the like.

[0130] In the present composition, the mixing ratio of the insecticidalorganophosphorus compound to the present imide compound, it may varywithin a range which the herbicidal activity of the present imidecompound can be increased, is usually 0.1:1 to 10000:1, preferably 1:1to 500:1, more preferably 1:1 to 100:1, much more preferably 2:1 to 25:1by weight.

[0131] The present composition may be usually used in the form offormulations such as emulsifiable concentrates, wettable powders,flowables, granules and the like which can be prepared by mixing withsolid carriers, liquid carriers, and the like, and if necessary, addingsurfactants, other adjuvants and the like.

[0132] In such a formulation, the present imide compound and theinsecticidal organophosphorus compound are usually contained at thetotal amount of 10 to 80% by weight.

[0133] The solid carrier to be used in the formulation may include, forexample, the following materials in fine powder or granule form: clays(e.g., kaolinite, diatomaceous earth, synthetic hydrated silicon oxide,Fubasami clay, bentonite, acid clay); talc and other inorganic minerals(e.g., sericite, powdered quartz, powdered sulfur, activated carbon,calcium carbonate); and chemical fertilizers (e.g., ammonium sulfate,ammonium phosphate, ammonium nitrate, ammonium chloride, urea). Theliquid carrier may include, for example, water; alcohols (e.g.,methanol, ethanol); ketones (e.g., acetone, methyl ethyl ketone,cyclohexanone); aromatic hydrocarbons (e.g., toluene, xylene,ethylbenzene, methylnaphthalene); non-aromatic hydrocarbons (e.g.,hexane, cyclohexane, kerosine); esters (e.g., ethyl acetate, butylacetate); nitrites (e.g., acetonitrile, isobutyronitrile); ethers (e.g.,dioxane, diisopropyl ether); acid amides (e.g., dimethylformamide,dimethylacetamide); and halogenated hydrocarbons (e.g., dichloroethane,trichloroethylene).

[0134] The surfactant may include, for example, alkylsulfric acidesters; alkylsulfonic acid salts; alkylarylsulfonic acid salts; theirpolyoxyethylene derivatives; polyethylene glycol ethers; polyhydricalcohol esters; and sugar alcohol derivatives.

[0135] The other adjuvants may include, for example, adhesive agents anddispersing agents, such as casein, gelatin, polysaccharides (e.g.,starch, gum arabic, cellulose derivatives, alginic acid), ligninderivatives, bentonite, and synthetic water-soluble polymers (e.g.,polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid); andstabilizers such as PAP (isopropyl acid phosphate), BHT(2,6-di-tert-butyl-4-methylphenol), BHA(2-/3-tert-butyl-4-methyoxyphenol), vegetable oils, mineral oils, fattyacids, and fatty acid esters.

[0136] The present composition can also be prepared by making each ofthe present imide compound and the insecticidal organophosphoruscompound into the above formulations; and then mixing theseformulations.

[0137] The present composition thus formulated may be applied to weedsor to a place where weeds are growing or will grow as such, or afterdiluted with water or the like.

[0138] Furthermore, the present composition can also be prepared bydiluting each formulations of the present imide compound and theinsecticidal organophosphorus compound with water or the like; and thenmixing these dilutions. Further, the present composition may also beused in admixture or be used together with other herbicides,insecticides, fungicides, plant growth regulators, fertilizers orsafener.

[0139] The present method is usually carried out by an application ofthe present composition, as such or after dilution, to weeds or to aplace where weeds grow or will grow, and also by application of thepresent imide compound (or its formulation) and the insecticidalorganophosphorus compound (or its formulation) together.

[0140] The application amounts of the present imide compound and theinsecticidal organophosphorus compound, although they may vary with themixing ratio of them, weather conditions, formulation types, applicationtimes, application methods, application places, and weeds to becontrolled, are usually 0.1 to 1000 g for the present imide compound and0.1 to 10000 g for the insecticidal organophosphorus compound perhectare. In the case of emulsifiable concentrates, wettable powders,flowables, or the like, they are usually applied after diluted in theirprescribed amounts with water at a ratio of 100 to 1000 liters perhectare.

[0141] The present method can be used, for example, in a corn field, awheat field, a barley field, a rice field, a sorghum field, a soybeanfield, a cotton field, a sugar beet field, a peanut field, a sunflowerfield, a rape field, an orchard and a paddy field.

EXAMPLE

[0142] The present invention is described in more detail with referenceto Formulation Examples and Test Examples, but the present invention isnot limited to these Examples.

[0143] The following will describe formulation examples, in which partsare by weight.

Formulation Example 1

[0144] Two and half (2.5) parts of flumiclorac-pentyl, flumioxazin orcinidon-ethyl, 42 parts of fenitrothion, fenthion, diazinon,chlorpyrifos, acephate, methidathion, disulfoton, dichlorvos, sulprofos,cyanophos, dimethoate, phenthoate, malathion, trichlorfon,azinphos-methyl, monocrotophos, ethion, thiometon, isoxathion,vamidothion, prothiofos or oxydeprofos, 50 parts of Solvesso (aromatichydrocarbon, produced by Exxon Mobil Chemical) and 5.5 parts of Sorpol3816 (anionic type and non-ionic type surfactants, produced by TohoChemical) are well stirred and mixed to give each emulsifiableconcentrate.

[0145] The following will describe test examples.

Evaluation Criteria

[0146] The herbicidal effect is evaluated with indices of 0 to 100 atintervals of 5, wherein “0” means that there was no or little differencein the degree of germination or growth between the treated plants andthe untreated plants at the time of examination, “100” means that thetest plants died completely.

Test Example 1

[0147] Fifty (50) parts of flumioxazin, 3 parts of Sorpol 5029-0(produced by Toho Chemical), 2 parts of Demol SNB and 45 parts ofShokozan Clay were well stirred and mixed to give 50% wettable powdersof flumioxazin. From the aqueous dilution of said 50% wettable powdersof flumioxazin, with a aqueous dilution of a emulsifiable concentrate offenitrothione (commercial name: Sumithion EC, produced by Agros),prepared aqueous dilution of the prescribed concentration of the presentformulation.

[0148] The aqueous dilution of the present formulation, with 1000 litersper hectare, were sprayed over a place in the orchard where common vetchand Carolina geranium (the height: about 40 to 55 cm) were growing.After 9 days from the application, the herbicidal activity wereexamined. The result are shown in Table 1. TABLE 1 Herbicidal activityDosage common Carolina Test Compound (g/hectare) vetch geraniumflumioxazin 60 10 50 flumioxazin + 60 + 1000 70 70 fenitrothione

Test Example 2

[0149] Fifty (50) parts of flumioxazin, 3 parts of Sorpol 5029-0(produced by Toho Chemical), 2 parts of Demol SNB and 45 parts ofShokozan Clay were well stirred and mixed to give 50% wettable powdersof flumioxazin. From the aqueous dilution of said 50% wettable powdersof flumioxazin, with a aqueous dilution of 40% wettable powders ofcyanophos (commercial name: Cyanox WP, produced by Agros), 25% wettablepowders of chlorpyrifos (commercial name: Dursban WP, produced by KumiaiChemical), 50% wettable powders of acephate (commercial name: Ortran WP,produced by Hokko Chemical), 36% wettable powders of methidathion(commercial name: Supracide WP, produced by Kumiai Chemical), 50%emulsifiable concentrate of phenthoate (commercial name: Elsan EC,produced by Nissan Chemical), 40% emulsifiable concentrate of diazinone(commercial name: Diazinon EC, produced by Hokko Chemical) or 50%emulsifiable concentrate of dichlorvos (commercial name: DDVP EC,produced by Takeda Pharmaceutical), prepared each aqueous dilution ofthe prescribed concentration of the present formulation.

[0150] Their aqueous dilution of the present formulation, with 1000liters per hectare, were sprayed over a place in the field where commoncocklebur (the height: about 55 cm) were growing. After 8 days from theapplication, the herbicidal activity were examined. The result are shownin Table 2. TABLE 2 Dosage Herbicidal Test Compound (g/hectare) activityflumioxazin 60 20 flumioxazin + 60 + 1000 75 cyanophos flumioxazin +60 + 1000 70 chlorpyrifs flumioxazin + 60 + 1000 35 acephateflumioxazin + 60 + 1000 40 methidathion flumioxazin + 60 + 1000 70phenthoate flumioxazin + 60 + 1000 80 diazinone flumioxazin + 60 + 100045 dichiorvos

Test Example 3

[0151] Fifty (50) parts of flumioxazin, 3 parts of Sorpol 5029-0(produced by Toho Chemical), 2 parts of Demol SNB and 45 parts ofShokozan Clay were well stirred and mixed to give 50% wettable powdersof flumioxazin. From the aqueous dilution of said 50% wettable powdersof flumioxazin, with a aqueous dilution of 25% emulsifiable concentrateof thiometon (commercial name: Ekatin EC, produced by Sankyo), 45%emulsifiable concentrate of oxydeprofos (commercial name: Estox EC,produced by Nihon Bayer Agrochem), 50% emulsifiable concentrate ofisoxathion (commercial name: Karphos EC, produced by Sankyo), 37% liquidof vamidothion (commercial name: Kilval Liq, produced by NissanChemical), 45% emulsifiable concentrate of prothiofos (commercial name:Tokuthion EC, produced by Nihon Bayer Agrochem), 50% emulsifiableconcentrate of fenthion (commercial name: Baycid EC, produced by NihonBayer Agrochem) or 50% emulsifiable concentrate of sulprofos (commercialname: Bolstar EC, produced by Nihon Bayer Agrochem), prepared eachaqueous dilution of the prescribed concentration of the presentformulation.

[0152] Their aqueous dilution of the present formulation, with 1000liters per hectare, were sprayed over a place in the field where commoncocklebur (the height: about 65 cm) were growing. After 4 days from theapplication, the herbicidal activity were examined. The result are shownin Table 3. TABLE 3 Dosage Herbicidal Test Compound (g/hectare) activityflumioxazin 60 30 flumioxazin + 60 + 1000 70 thiometon flumioxazin +60 + 1000 70 oxydeprofos flumioxazin + 60 + 1000 70 isoxathionflumioxazin + 60 + 1000 65 vamidothion flumioxazin + 60 + 1000 70prothiofos flumioxazin + 60 + 1000 65 fenthion flumioxazin + 60 + 100070 sulprofos

Test Example 4

[0153] Ten (10) parts of flumiclorac-pentyl were dissolved in 80 partsof xylene, after adding 10 parts of Sorpol 3005X (produced by TohoChemical), the solution was well stirred and mixed to give 10%emulsifiable concentrate of flumiclorac-pentyl. From the aqueousdilution of said 10% emulsifiable concentrate of flumiclorac-pentyl,with a aqueous dilution of 25% emulsifiable concentrate of thiometon(commercial name: Ekatin EC, produced by Sankyo), 45% emulsifiableconcentrate of oxydeprofos (commercial name: Estox EC, produced by NihonBayer Agrochem) or 50% emulsifiable concentrate of fenthion (commercialname: baycid EC, produced by Nihon Bayer Agrochem), prepared eachaqueous dilution of the prescribed concentration of the presentformulation.

[0154] Their aqueous dilution of the present formulation, with 1000liters per hectare, were sprayed over a place in the field where commoncocklebur (the height: about 65 cm) were growing. After 4 days from theapplication, the herbicidal activity were examined. The result are shownin Table 4. TABLE 4 Dosage Herbicidal Test Compound (g/hectare) activityflumiclorac-pentyl 100 30 flumiclorac-pentyl + 100 + 1000 50 thiometonflumiclorac-pentyl + 100 + 1000 60 oxydeprofos flumiclorac-pentyl +100 + 1000 70 fenthion

Industrial Applicability

[0155] The present composition have excellent herbicidal effect againsta variety of weeds.

What is claimed:
 1. A herbicidal composition containing: (i) anN-phenyltetrahydrophthalimide compound represented by Chemical Formula(1):

 wherein R¹ represents hydrogen or halogen; R² represents halogen and R³represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl, or R² and R³represent together —O—CHR⁴—C(═O)—NR⁵—, whose oxygen connected to4-position of the benzene ring, whose nitrogen connected to 5-positionof the benzene ring and wherein R⁴ represents hydrogen or methyl and R⁵represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or (C1-C3 alkoxy)C1-C3 alkyl, and (ii) an effective amount for increasing activity of theN-phenyltetrahydrophthalimide compound of an insecticidalorganophosphorus compound.
 2. The herbicidal composition according toclaim 1, wherein a weight ratio of the insecticidal organophosphoruscompound to the N-phenyltetrahydrophthalimide compound is 0.1:1 to10000:1.
 3. The herbicidal composition according to claim 1, wherein R¹is hydrogen or fluorine, R² and R³ are together —O—CH₂—C(═O)—NR⁵—, inwhich R⁵ is C3-C6 alkynyl.
 4. The herbicidal composition according toclaim 1, wherein R¹ is fluorine, R² is chlorine and R³ is (C1-C8alkoxy)carbonyl C1-C2 alkoxy.
 5. The herbicidal composition according toclaim 1, wherein the N-phenyltetrahydrophthalimide compound isflumioxazin, flumiclorac-pentyl or cinidon-ethyl.
 6. The herbicidalcomposition according to claim 1, wherein the insecticidalorganophosphorus compound is represented by Chemical Formula (6):

wherein X¹ represents oxygen or sulfur, X² represents oxygen, sulfur ordirect bond between phosphorous atom and R⁸ in the Chemical Formula (6),R⁶ represents lower alkyl, R⁷ represents lower alkoxy, lower alkylthio,lower alkylcarbonylamino or phenyl, R⁸ represents optionally substitutedalkyl, optionally substituted alkenyl, optionally substituted phenyl oroptionally substituted heteroaryl.
 7. The herbicidal compositionaccording to claim 1, wherein the insecticidal organophosphorus compoundis fenitrothion, fenthion, diazinon, chlorpyrifos, acephate,methidathion, disulfoton, dichlorvos, sulprofos, cyanophos, dimethoate,phenthoate, malathion, trichlorfon, azinphos-methyl, monocrotophos,ethion, thiometon, isoxathion, vamidothion, prothiofos or oxydeprofos.8. A method for controlling weeds, which comprises applying (i) anN-phenyltetrahydrophthalimide compound represented by Chemical Formula(1):

 wherein R¹ represents hydrogen or halogen; R² represents halogen and R³represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl, or R² and R³represent together —O—CHR⁴—C(═O)—NR⁵—, whose oxygen connected to4-position of the benzene ring, whose nitrogen connected to 5-positionof the benzene ring and wherein R⁴ represents hydrogen or methyl and R⁵represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or (C1-C3 alkoxy)Cl-C3 alkyl, with (ii) an effective amount for increasing activity ofthe N-phenyltetrahydrophthaiimide compound of the insecticidalorganophosphorus compound, to weeds or to a place where weeds aregrowing or will grow.
 9. The method for controlling weeds according toclaim 8, wherein a weight ratio of the insecticidal organophosphoruscompound to the N-phenyltetrahydrophthalimide compound is from 0.1:1 to10000:1.
 10. The method according to claim 8, wherein R¹ is hydrogen orfluorine, R² and R³ are together —O—CH₂—C(═O)—NR⁵—, in which R⁵ is C3-C6alkynyl.
 11. The method according to claim 8, wherein R¹ is fluorine, R²is chlorine and R³ is (C1-C8 alkoxy)carbonyl C1-C2 alkoxy.
 12. Themethod according to anyone of claims 8, wherein the insecticidalorganophosphorus compound is represented by Chemical Formula (6):

wherein X¹ represents oxygen or sulfur, X² represents oxygen, sulfur ordirect bond between phosphorous atom and R⁸ in the Chemical Formula (6),R⁶ represents lower alkyl, R⁷ represents lower alkoxy, lower alkylthio,lower alkylcarbonylamino or phenyl, R⁸ represents optionally substitutedalkyl, optionally substituted alkenyl, optionally substituted phenyl oroptionally substituted heteroaryl.